Diisopropylethylamine → HCID 117842945, compound

HRID 2209165Notes

Reaction equation

HRID 2209165 reaction equation
[CH3:1][N:2]1[C:6]2[C:7]([O:23][C@@H:24]([C@H:26]3[CH2:30][NH:29][C:28](=[O:31])[CH2:27]3)[CH3:25])=[N:8][C:9]([C:11]3[CH:12]=[N:13][C:14]([N:17]4[CH2:22][CH2:21][NH:20][CH2:19][CH2:18]4)=[CH:15][CH:16]=3)=[CH:10][C:5]=2[N:4]=[CH:3]1.CCN(C(C)C)C(C)C.[O:41]1[CH2:44][C:43](=O)[CH2:42]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>C1COCC1.CO.ClCCl>[CH3:1][N:2]1[C:6]2[C:7]([O:23][C@@H:24]([C@H:26]3[CH2:30][NH:29][C:28](=[O:31])[CH2:27]3)[CH3:25])=[N:8][C:9]([C:11]3[CH:12]=[N:13][C:14]([N:17]4[CH2:22][CH2:21][N:20]([CH:43]5[CH2:44][O:41][CH2:42]5)[CH2:19][CH2:18]4)=[CH:15][CH:16]=3)=[CH:10][C:5]=2[N:4]=[CH:3]1

Participants

7

Reactant 4

HCID 81531DiisopropylethylamineHCID 5049666Sodium triacetoxyborohydrideHCID 150242543-OxetanoneHCID 117842917HCID 117842917, compound

Product 1

HCID 117842945HCID 117842945, compoundYield 22.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 21226129Dichloromethane methanolSolvent

Procedure

(R)-4-((R)-1-((3-methyl-6-(6-(piperazin-1-yl)pyridin-3-yl)-3H-imidazo[4,5-c]pyridin-4-yl)oxy)ethyl)pyrrolidin-2-one (130 mg, 0.31 mmol) was dissolved in THF (7.71 ml), followed by the addition of Hunig's base (0.05 ml, 0.31 mmol), 3-oxetanone (0.2 ml, 3.08 mmol), sodium triacetoxyborohydride (228.79 mg, 1.08 mmol) and stirred at 50 C for 90 minutes. The reaction was diluted with 25% methanol/dichloromethane, washed with water, dried, filtered and concentrated. Residues were purified by silica gel column chromatography to yield the (R)-4-((R)-1-((3-methyl-6-(6-(4-(oxetan-3-yl)piperazin-1-yl)pyridin-3-yl)-3H-imidazo[4,5-c]pyridin-4-yl)oxy)ethyl)pyrrolidin-2-one (32.9 mg, 22%)

Workup

  1. washwashed with water
  2. customdried
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customResidues were purified by silica gel column chromatography

Sources & evidence

ORD record
ord-1434fb4f08a04e3e996bf98e58605517
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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